HCID 67900749, compound → HCID 19876046, compound

HRID 1886469Notes

Reaction equation

HRID 1886469 reaction equation
[C:1]([O:4][C:5]1[CH:35]=[CH:34][CH:33]=[CH:32][C:6]=1[C:7]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][N:19]3[C:23]4=[N:24][C:25]([CH3:29])=[CH:26][C:27]([CH3:28])=[C:22]4[N:21]=[C:20]3[CH2:30][CH3:31])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)=[O:8])(=[O:3])[CH3:2]>O1CCOCC1>[C:1]([O:4][C:5]1[CH:35]=[CH:34][CH:33]=[CH:32][C:6]=1[C:7]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][N:19]3[C:23]4=[N:24][C:25]([CH3:29])=[CH:26][C:27]([CH3:28])=[C:22]4[N:21]=[C:20]3[CH2:30][CH3:31])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)=[O:8])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 67900749HCID 67900749, compound

Product 1

HCID 19876046HCID 19876046, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a refluxing solution of 220 mg (0.47 mmol) of the product of Example 19 in 5 mL of 1,4-dioxane was added 320 mg (1.41 mmol, 3.0 eq) of 2,3-dichloro-5,6-dicyano-1,4-quinone. The mixture was refluxed for 6 hours then cooled and concentrated in vacuo. The resultant oil was flash chromatographed with ethyl acetate to yield 50 mg (23%) of the titled compound as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. temperaturethen cooled
  3. concentrationconcentrated in vacuo
  4. customchromatographed with ethyl acetate

Sources & evidence

ORD record
ord-6de977684d224d0587a843197972a226
Source dataset
uspto-grants-1992_09
Patent number
US05151435

Reaction notes

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